#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151817.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151817 loop_ _publ_author_name 'Bradley, Stephen A.' 'Bresnan, Brian J.' 'Draper, Sylvia M.' 'Geraghty, Niall W. A.' 'Jeffares, Mark' 'McCabe, Thomas' 'McMurry, T Brian H' 'O'Brien, John E' _publ_section_title ; Photochemical [2 + 2] cycloaddition reactions of 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation control to account for exceptions to the "rule of five". ; _journal_issue 8 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2959 _journal_page_last 2968 _journal_volume 9 _journal_year 2011 _chemical_formula_sum 'C18 H20 O3' _chemical_formula_weight 284.34 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 102.795(8) _cell_angle_beta 99.112(11) _cell_angle_gamma 105.356(9) _cell_formula_units_Z 2 _cell_length_a 6.6572(9) _cell_length_b 9.8399(8) _cell_length_c 12.3209(15) _cell_measurement_temperature 293(2) _cell_volume 738.47(16) _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2763 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 1.74 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details Sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.161 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 2529 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.991 _refine_ls_R_factor_all 0.1289 _refine_ls_R_factor_gt 0.0513 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1022 _refine_ls_wR_factor_ref 0.1254 _reflns_number_gt 1396 _reflns_number_total 2529 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0ob01131b.txt _[local]_cod_data_source_block mcmcs _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_original_cell_volume 738.47(15) _cod_database_code 7151817 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.7039(4) 0.4912(2) 0.85995(18) 0.0592(6) Uani 1 1 d . . . O3 O 1.0758(3) 0.7487(2) 0.85689(17) 0.0540(6) Uani 1 1 d . . . C1 C 0.7874(5) 0.9930(3) 0.7799(3) 0.0498(8) Uani 1 1 d . . . C2 C 0.9085(5) 0.8787(3) 0.7491(2) 0.0411(7) Uani 1 1 d . . . C3 C 0.9182(4) 0.7822(3) 0.8251(2) 0.0377(6) Uani 1 1 d . . . C4 C 0.7099(4) 0.7317(3) 0.8622(2) 0.0383(7) Uani 1 1 d . . . C5 C 0.5167(5) 0.6683(3) 0.7568(2) 0.0437(7) Uani 1 1 d . . . C6 C 0.5833(5) 0.6578(3) 0.6430(3) 0.0454(7) Uani 1 1 d . . . C7 C 0.7344(4) 0.8013(3) 0.6340(2) 0.0413(7) Uani 1 1 d . . . C8 C 0.6473(6) 0.9346(4) 0.6577(3) 0.0563(9) Uani 1 1 d . . . C9 C 0.6708(6) 0.9856(4) 0.8781(3) 0.0549(9) Uani 1 1 d . . . C10 C 0.6976(6) 0.8732(3) 0.9416(3) 0.0506(8) Uani 1 1 d . . . C11 C 0.7300(5) 0.6225(3) 0.9294(3) 0.0471(7) Uani 1 1 d . . . C12 C 0.7199(6) 0.3774(4) 0.9134(3) 0.0760(11) Uani 1 1 d . . . H12A H 0.8675 0.3928 0.9464 0.114 Uiso 1 1 calc R . . H12B H 0.6618 0.2838 0.8572 0.114 Uiso 1 1 calc R . . H12C H 0.6411 0.3796 0.9723 0.114 Uiso 1 1 calc R . . C13 C 0.8166(5) 0.7693(3) 0.5268(2) 0.0446(7) Uani 1 1 d . . . C14 C 0.7222(6) 0.7913(4) 0.4269(3) 0.0608(9) Uani 1 1 d . . . C15 C 0.7899(7) 0.7504(4) 0.3268(3) 0.0725(11) Uani 1 1 d . . . C16 C 0.9495(7) 0.6879(4) 0.3256(3) 0.0681(10) Uani 1 1 d . . . C17 C 1.0459(6) 0.6671(4) 0.4243(3) 0.0687(10) Uani 1 1 d . . . C18 C 0.9802(5) 0.7077(4) 0.5244(3) 0.0583(9) Uani 1 1 d . . . H1 H 0.884(5) 1.093(3) 0.796(2) 0.055(8) Uiso 1 1 d . . . H2 H 1.048(4) 0.928(3) 0.7394(19) 0.036(7) Uiso 1 1 d . . . H5A H 0.442(4) 0.568(3) 0.754(2) 0.045(7) Uiso 1 1 d . . . H5B H 0.422(4) 0.729(3) 0.763(2) 0.048(8) Uiso 1 1 d . . . H6A H 0.654(4) 0.576(3) 0.629(2) 0.051(8) Uiso 1 1 d . . . H6B H 0.455(5) 0.625(3) 0.581(2) 0.058(9) Uiso 1 1 d . . . H8A H 0.504(5) 0.908(3) 0.647(2) 0.050(9) Uiso 1 1 d . . . H8B H 0.689(6) 0.993(4) 0.608(3) 0.084(12) Uiso 1 1 d . . . H9A H 0.717(5) 1.078(4) 0.930(3) 0.065(10) Uiso 1 1 d . . . H9B H 0.521(5) 0.972(3) 0.844(2) 0.066(10) Uiso 1 1 d . . . H10A H 0.832(5) 0.915(3) 1.005(2) 0.057(9) Uiso 1 1 d . . . H10B H 0.586(6) 0.845(3) 0.977(3) 0.075(11) Uiso 1 1 d . . . H14 H 0.600(5) 0.831(3) 0.424(2) 0.064(10) Uiso 1 1 d . . . H15 H 0.726(5) 0.772(3) 0.264(3) 0.064(9) Uiso 1 1 d . . . H16 H 0.993(6) 0.656(4) 0.249(3) 0.101(12) Uiso 1 1 d . . . H17 H 1.158(6) 0.616(4) 0.421(3) 0.099(13) Uiso 1 1 d . . . H18 H 1.059(5) 0.695(3) 0.597(3) 0.065(9) Uiso 1 1 d . . . O1 O 0.7681(4) 0.6501(3) 1.03156(19) 0.0720(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0734(15) 0.0445(13) 0.0732(15) 0.0273(12) 0.0255(12) 0.0263(11) O3 0.0432(12) 0.0667(14) 0.0632(14) 0.0251(11) 0.0184(10) 0.0258(11) C1 0.062(2) 0.0339(17) 0.057(2) 0.0121(15) 0.0207(17) 0.0170(16) C2 0.0380(17) 0.0380(15) 0.0475(18) 0.0124(14) 0.0162(14) 0.0080(14) C3 0.0365(16) 0.0379(15) 0.0341(15) 0.0004(12) 0.0074(13) 0.0123(13) C4 0.0375(16) 0.0406(15) 0.0424(16) 0.0129(13) 0.0160(13) 0.0164(13) C5 0.0370(17) 0.0368(17) 0.059(2) 0.0134(14) 0.0135(15) 0.0137(14) C6 0.0409(18) 0.0428(17) 0.0491(19) 0.0086(14) 0.0073(16) 0.0125(15) C7 0.0417(16) 0.0389(16) 0.0457(17) 0.0133(13) 0.0102(14) 0.0150(13) C8 0.057(2) 0.055(2) 0.067(2) 0.0259(18) 0.0152(19) 0.0271(18) C9 0.066(2) 0.0439(19) 0.063(2) 0.0106(17) 0.0251(19) 0.0282(18) C10 0.055(2) 0.0470(18) 0.055(2) 0.0101(16) 0.0254(19) 0.0194(16) C11 0.0431(17) 0.0549(19) 0.054(2) 0.0203(16) 0.0219(16) 0.0220(15) C12 0.074(2) 0.064(2) 0.120(3) 0.058(2) 0.036(2) 0.037(2) C13 0.0534(18) 0.0433(16) 0.0377(17) 0.0142(13) 0.0119(14) 0.0128(14) C14 0.066(2) 0.069(2) 0.050(2) 0.0244(18) 0.0084(18) 0.0211(19) C15 0.084(3) 0.083(3) 0.045(2) 0.031(2) 0.007(2) 0.009(2) C16 0.083(3) 0.065(2) 0.053(2) 0.0149(18) 0.030(2) 0.010(2) C17 0.076(3) 0.076(3) 0.059(2) 0.0138(19) 0.028(2) 0.028(2) C18 0.065(2) 0.072(2) 0.047(2) 0.0156(17) 0.0181(18) 0.0321(19) O1 0.0897(18) 0.0939(18) 0.0542(15) 0.0322(13) 0.0272(13) 0.0487(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 C12 116.6(2) . . ? C8 C1 C9 116.9(3) . . ? C8 C1 C2 89.4(2) . . ? C9 C1 C2 117.7(2) . . ? C3 C2 C1 116.3(2) . . ? C3 C2 C7 113.1(2) . . ? C1 C2 C7 89.3(2) . . ? O3 C3 C2 124.1(3) . . ? O3 C3 C4 123.1(2) . . ? C2 C3 C4 112.7(2) . . ? C11 C4 C3 108.3(2) . . ? C11 C4 C10 110.0(2) . . ? C3 C4 C10 103.7(2) . . ? C11 C4 C5 113.0(2) . . ? C3 C4 C5 110.6(2) . . ? C10 C4 C5 110.9(2) . . ? C6 C5 C4 113.2(2) . . ? C5 C6 C7 114.8(2) . . ? C13 C7 C6 109.0(2) . . ? C13 C7 C8 117.8(2) . . ? C6 C7 C8 114.3(3) . . ? C13 C7 C2 116.3(2) . . ? C6 C7 C2 109.8(2) . . ? C8 C7 C2 88.4(2) . . ? C1 C8 C7 90.9(2) . . ? C10 C9 C1 116.2(3) . . ? C9 C10 C4 112.5(3) . . ? O1 C11 O2 124.0(3) . . ? O1 C11 C4 124.9(3) . . ? O2 C11 C4 111.1(3) . . ? C14 C13 C18 118.1(3) . . ? C14 C13 C7 121.3(3) . . ? C18 C13 C7 120.5(3) . . ? C13 C14 C15 120.3(4) . . ? C16 C15 C14 120.8(4) . . ? C15 C16 C17 119.4(4) . . ? C16 C17 C18 120.3(4) . . ? C13 C18 C17 121.1(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C11 1.332(3) . ? O2 C12 1.438(3) . ? O3 C3 1.214(3) . ? C1 C8 1.535(5) . ? C1 C9 1.542(4) . ? C1 C2 1.565(4) . ? C2 C3 1.479(4) . ? C2 C7 1.571(4) . ? C3 C4 1.521(4) . ? C4 C11 1.515(4) . ? C4 C10 1.544(4) . ? C4 C5 1.555(4) . ? C5 C6 1.527(4) . ? C6 C7 1.539(4) . ? C7 C13 1.510(4) . ? C7 C8 1.558(4) . ? C9 C10 1.521(4) . ? C11 O1 1.197(3) . ? C13 C14 1.380(4) . ? C13 C18 1.380(4) . ? C14 C15 1.391(5) . ? C15 C16 1.362(5) . ? C16 C17 1.365(5) . ? C17 C18 1.385(4) . ? _journal_paper_doi 10.1039/c0ob01131b